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Lev Leshchenko was born on 1 February 1942 in Moscow, Soviet Union. His father, Valerjan Andreevich (1904–2004), was a Red Army officer who was at war outside of Moscow. He was accorded with medals for participation in the Second World War. His mother, Claudia Petrovna Leshchenko (1915 to 1943), died shortly after Leshchenko was born. His grandparents, along with his stepmother Irina Pavlovna Leshchenko, whom his father remarries in 1948, brought Leshchenko up in Sokolniki, Moscow. It was during his childhood when he was influenced from classical music and theatre, and began performing popular songs of Leonid Utyosov.[1]

Between 1960 and 1959, Leshchenko worked as a stage helper at the State Academic Bolshoi Theatre, and before being conscripted into the army in 1961, he worked as an adjuster at a precision measuring instrument factory. Leschenko served in the mechanical vehicle division of the Soviet Army, positioned in the German Democratic Republic. On 27 January 1962, Leshchenko (then a private) became a soloist within the Soviet Red Army Ensemble, and received the offer to remain in the army. Leshchenko accepted every role offered to him by the ensemble, namely singing in a quarter, conducting concerts and even reading verses, where it is often said to have begun his entertainment career. At the same time, he was preparing for theatrical examinations for Russian Academy of Theatre Arts (abbreviated as GITIS), the most renowned theatrical school of the Soviet Union, which he passed and was successfully admitted to in September 1964.[2]

Leshchenko began touring with concert bands, visiting some of the more isolated parts of the country. In 1969, Leshchenko was admitted as a member of the Moscow Operetta Theatre. He experienced with many roles, but was aware of his musical gift, and was constantly seeking for soloist acts. On 13 February 1970, having successfully gone through a contest held by the state radio station, Leshchenko became a solo vocalist for the Soviet state radio station.

In 1975, Leshchenko became the first singer who dared to perform "Den Pobedy" (an immensely popular Soviet song dedicated to the Victory Day, which was initially disliked by the authorities due to the unconventional music style). His rendition has become by far the most successful.